Plant growth regulating compositions including cyanoalkylamino substituted triazines

ABSTRACT

Herbicidal composition comprising, in an agriculturally acceptable carrier, compounds of the formula   WHEREIN X is a halogen atom, lower alkoxy, lower alkyl mercapto,   BEING HYDROGEN, LOWER ALKYL, LOWER ALKENYL, OR LOWER ALKYL OR ALKENYL SUBSTITUTED WITH -OH, -OR, -SR or -CN, R being lower alkyl, and wherein one of R3 and R4 is alkyl or alkenyl having from one to eight carbon atoms and wherein R3 and R4 together with the adjoining carbon atom form a five to seven membered cycloalkyl ring; and a method of regulating growth of plants therewith.

United States Patent [72] Inventor Werner Schwarze Franklurt am Main, Germany l2l] Appl. No. 884,733 [22] Filed Dec. 12, I969 [45] Patented Nov. I6, 1971 [73] Assignee Deutache Gold-und Sllber-Sebeldeanstalt Vormais Roeasler Franltiurt am Main, Germany I32] Priorities July 16, 1966 [33] Germany [31 D 50 605;

Nov. 22, 1966, Germany, No. D 51 608 Original application Nov. 20, 1967, Ser. No. 684,514, now Patent No. 3,505,325, continuation-impart of Ser. No. 652,036, July 10, 1967, abandoned.

[5| Int. Cl "Li it; A0 lm 9/22 [50] Field of Search 71/93 i 5 6] References Cited UNITED STATES PATENTS 3,4l5,827 l2/l968 Nikles et al 71/93 X 3,488,l8l l/l970 Nikles 71/93 [54] PLANT GROWTH REGULATING COMPOSITIONS INCLUDING CYANOALKYLAMINO SUBSTITUTED TRIAZINES 17 Claims, No Drawings [52] U.S.Cl 71/93,

r Primoiy Eiaminer-James 0. Thomas, .I r. Attorney-Michael S. Striker I ABSTRACT: Herbicidal composition comprising, in an agricultnraliy acceptable canier, compounds of the formula wherein X is a halogen atom, lower alkoxy, lower alkyl mercapto,

, R and R being hydrogen, lower alkyl, lower alkenyl, or lower alkyl or alkenyi substituted with OH, 0R, -SR or CN, R being PLANT GROWTH REGULATING'COMPOSITIONS INCLUDING CYANOALKYLAMINO SUBSTITUTED TRIAZINES C ROSS-REFERENC ES TO RELATED APPLICATIONS This application is a division of application, Ser. No. 684,5!4 filed by the same inventor in respect of NOVEL Cr'ANOALKYLAMlNO SUBSTITUTED TRIAZINES HAV- ING PLANT GROWTH REGULATING ACTION," on Nov. 20, i967, now US. Pat. No. 3,505,325 which latter application, in turn, was a continuation-in-part of application, Ser. No. 652,036, filed by the same inventor on July 10, I967 and which now is abandoned.

BACKGROUND OF THE INVENTION The invention relates to compositions in which the effective agents are cyanoalkylamino substituted s-triazines having plant growth regulating and, especially, herbicidal properties.

Herbicides have become known which contain an s-triazine ring and in the 2-position carry an azido or alkyl mercapto group or halogen and in 4-position carry a cyanoalkylamino group as active ingredient (Belgian Pat. Nos. 656,233 and 644,355). However, in these compounds the cyano group is directly attached to a primary carbon atom and compounds of this type do not reach the activity of the best productsavailable commercially.

A number of herbicidal substituted bisalkylamino triazines have also become known. Some have, in practice, been found to be excellent herbicides, such as, for. example, 2,4-bisethylamino-o-chloro-triazine, '2-ethylamino-4- isopropylamino--chlorotriazine, I 2-m'ethylamino-4 isopropylamino-6-methylmercapto-triazine and 2,4-bisisopropylamino-o-methylmercaptotriazine. These 1 compounds all contain two alkyl amino groups. 2-amino-4-alkylamino-triazines with strong herbicidal activity have not become known.

SUMMARY OF THE INVENTION The invention concerns a plant growth regulating composition which comprises (a) a cyanoalkylamino substituted triazine oftheformula M k wherein X is a halogen atom, lower alkoxy, lower alkyl mer- CHPIO, R1

, R and It nil being hydrogen or lower alkyl or alkenyl or lower alkyl or alkenyl substituted with -OH, -OR, -SR or -CN, R being lower alkyl, and wherein one of R and R is alkyl or alkenyl having from one to eight carbon atoms and wherein R and R together with the adjoining carbon atom form a five to seven membered ring and (b) an agriculturally acceptable carrier for said triazine compound.

The invention also embraces a method of regulating or controlling the growth of plants with these compositions.

DESCRIPTION OF THE PREFERRED EMBODIMENTS According to the invention it was found that cyanoalkylamino-s'triazines as described above in which the cyano group is directly connected to a secondary or preferably a tertiary carbon atom which is also directly attached to the amino group on the triazine ring are marked by their especially high and selective herbicidal activity and are rapidly decomposed in the soil. In the description the term lower" as in lower alkyl, lower alkoxy and lower alkenyl is intended to signify groups with one to four carbon atoms.

-in the presence of-ahydrogen halide binding agent, such as aqueous NaOH and-subsequently with 1 mol ofammonia or amine of theformula NHRR, also in the presence of 1 mol of aqueous NaOH. Suitednitrile for this purpose, for example,

are:

The

lIsC

NII:

1130 Nm N IIzC NIIz

IIr-CII-z 0N CH NH:

ClI- -CII These alpha-nitriles are produced by conventional methods, such as, for instance, by first reacting ketones or aldehydes withhydrocyanicacid in the presence of an alkaline catalyst toform. thecorresponding cyano hydrine and reacting the latter with ammonia to produce the desired amino nitrile. The synthesis also can be carried out in one process step by reacting the ketone or aldehyde,.hydrocyanic acid and ammonia with or. without a.diluent. A mixture of ammonium chloride and alkali-metal cyanide can be used instead of free hydrocyanic acid. In the latter instance the reaction is carried out in the presence of water. The alpha-amino nitriles are water white liquids which can be distilled under vacuum. They are relatively unstable but can be kept in a refrigerator (0 C.) for several days without decomposition.

The alkyl mercapto derivatives can, for instance, be produced by reaction of the corresponding chloro substituted triazineswith an alkyl mercaptan in the presence of an acid binding agent. It is also possible-to start from 2*alkyl-mercap' to-4,6-dichlorotriazines which are sequentially reacted with an amino nitrile in the presence of an acid binding agent and in the-presence of an amine again in the presence of an acid binding'agent. It furthermore is possible first to introduce an amino group into the triazine and then the alkyl mercapto group andfinally again an amino group (starting, for instance,

- from cyanuric chloride).

.The. alkoxy derivatives, for instance, can be produced in high yields by reacting the corresponding'chloro substituted triazines with sodium or potassium alcoholates in an alcohol at raised temperatures and, if desired. raised-pressures. The cyanuric chloride also can first be converted to the 2-alkoxy- 2,4'dichlorotriazine by conventional methods, for example, by reacting of cyanuric chloride with alcohol in collidine and then reacting the intermediate with the amino nitrile and the amine in any desired sequence. lt is'also possible analogously to'start with a 2-alkyl-amino-2,4-chlorotriazine and reacting this withanalcohol and with an amino nitrile in any desired sequence.

Azido triazines of the type concerned can be produced by reaction of chlorotriazine with an alkali metal or ammonium azide in dimethyl formamide or dimethyl sulfoxide or even better by reacting such azides with a quartemary methyl ammonium compound in water.

'fhe compounds are marked by their superior herbicidal properties and can be used as preemergence or postemcrgence herbicides. They are already able to influence the growth of plants when applied in low concentrations. Depend- 5 ing upon the nature of substituents R to R, they can be used for the destruction or selective suppression of weeds among cultured plants, as well as for the total destruction and prevention of undesired plant growth.

The compositions of the invention can also be used, for example, for defoliation, reduction of set of fruit, delay in flowering. They can be used individually or in admixture with each other or also with insecticides, fungicides and fertilizers.

The following is a tabulation of compounds according to the invention having the structural formula given in the Summary of the Invention with the substituentX and R to R indicated.

Melting X R B. R R point, C. Appearance H H CH; CH; 191-192 white crystals. H H CH CzHs 178-179 D0. H CH: CH3 CH3 201-202 D0 H CH; CH; C 115 151-152 Do H CH: CH: C(H0-1 141-142 D0 H CH; CgHr C 115 177-178 D0 C1 t 11 CH: /CH:-C1la\ C C111 1 3-184 I)".

CzHs CH3 CH3 161-162 D0. 01H; CH3 C1115 136-137 D0.

021-15 CH1 /CH:

C1 H CaHs CHr-CH:

C CH: 134-136 D0.

CH -C H:

H C2Hs Cal-I5 CzHs 161-162 D0. H CaHI-i CH: CH: 188-189 D0. H CsHr-l CH; CzHs 156 D0. H CsH1-l CH3 C;H -n 148-149 D0. H C H11 CH3 CIHO1 121 D0. H CqHo-n CH3 CH3 149-160 Du. H CHzCHzCHaOCI-Is CH: CH: 124-125 Do. 7 H CHgCHgSCH: CH; CH; 127-129 D0. H CHzCN CH; CH; 166-167 D0. H CHrCHaOH CH: C11; 148-149 Do. H CHrCH=CHz CH; C11; 136-138 D0. H CH: CH: C11: 124-125 D0. 11 CgHrl CH: C113 141-143 D0. 11 CH: C2115 C2115 118-120 Do. H CsH1-1 C2115 C 115 103-105 D0. 11 CH1C H5 011: CH; 126-128 D0. H CHrCH- -CH: CH: CH: 83-85 D0. H CHzCHzOH CH3 CH3 99-100 D0.

CHr-CHz SCH; H C 11 C CH; 113-115 Do.

CH1CI1:|

OCH; H CH: CzHs CgHs 129-131 D0 0011: H CH; CH; CH: 103-104 D0 0011; H CH1; CH; CH: 91-92 Do 0011; H C1115 C7115 C 115 00-01 DO Na 11 CH; C 11s C": 132-134 D0 Ni 11 il i- "Us CH: 5 l

Melting R R R R point, 0. Appearance C Hz- C H: SCH; H CH; C CH 139-141 DO.

C HICH2 /C Ila-CH: C3H1-i C C H2 127-128 DO.

C HzC Hz 02H; CH3 CH3 126-127 D0. 02H! H1 CzHs 83-84 D0. 2 C H; CH: 96-97 Do. 62H CH: 02H; 71-72 D0. H CH; CH: 193 D0. 02H CH3 CH3 102-105 DO. (CH2)I0 C H; CH; C H; 92-93 Do. H C H; CzHs 128-130 D0. (13111-1 C H; C 115 69-70 Do. g Qa a CH; CzHs 78-79 D0. CH3 CJH'I-i 164-165 DU. (CHzhO CH3 CH C3H -i 109-111 D0. C H; 0 H3 C|Hri 130 D0. C H; C Hg em -n 97-93 D0. C H; C H: csHn-l 105 Do. 02H: CH; CsHn-i 120 Do.

s K /C\ /C H: 201 Do.

C Hg C Hz C111; C11 CgH 85-87 Do. C lh-l C111 C 11 D0. Ii C H; H 198-200 Do. CgHy-l C II: 200-201 D0. C 115 i-CgH D0. CsH1-l l-C H1 D0. ilia n-CgH Do. -CHg-CHa-CH:OCH3 CH3 D0. JH'l-l C H; Do. --CHz-CH1CHz-OCH3 CH D0. C2115 CH3 D0. CzHs C H: DO. (hHJ-i CH: (3 H; on; Do. -CHg-CHr-CHz-OOH3 CH3 D0. CH: CH; D0. 2H; CzHs D0. CH3 Cgflr D0. 02H: o s

It was very surpnstng and unexpected that the trtaztnes ac- {5 I n a 2 a 3 cording to the invention whtch contatn a tertiary or secondary g 5 8%? l W C atom attached directly to an amino group and directly to a cyano group would be extremely string herbicides as corresponding compounds containing a carboxamide, a carboxy or a carboalkoxy group instead of the cyano group, such as for instance 2-chloro-4-ethylamino-6-( l )-methyi- 1 -carbamoylethyl)-amino-s-triazine and 2chloro-4-ethylamino-6- l-methyll -carboxy-ethyl )-amino-s-triazine have no phytotoxic action whatsoever.

The excellent herbicidal action of the compounds according to the invention therefore depends upon the presence of the cyano group which must be bound directly to a tertiary or a secondary C atom. Cyanoalkylamino triazines which carry the group NH-(CH,),-CN are much less active.

The chlorotriazines which have been introduced in practice have a long persistence in soil, which often is undesired. in comparison therewith the triazines according to the invention are decomposed in soil in a relatively short period of time.

The chlorotriazines according to the invention are very selective in corn cultures. in this connection they, for example, resemble 2,4-bis-ethylamino-fi-chloro-triazine. However, they have the advantage over this compound in that they are decomposed in the soil to substances without herbicidal action after only one culture period. it therefore is not necessary to sow corn again in the same fields in the following year.

The compounds according to the invention with the following suhstituents have good selectivity in corn cultures:

The selectivity of the compounds according to the invention, however, is not restricted to corn. They also have herbicidal selectivity in cultures other than corn, depending on their constitution as illustrated by way of example by the following: (selective in wheat) Selective in wheat c1 II 03117-1 H (flirt Cl H CH; Call: 2: SCH: Ii CH3 CH3 ('gllri Selective in rice CH3 CH3 CJuT' Cl!:- CH3 0 C":

Clig-Cli! CII:CH=C1I: (Ill; Cli; Cells UH: Cells Selective in cotton SCH; 1i CgIIq-i Ull (H1 SCH3.. Y H CH (4H5 (1:115 OCH: II Calls CH1 (H SCH3....... Ii Cali ("'1 (H1 The compounds according to the invention, depending upon their substituents. display an outstanding prccntergcncc und/or postcmcrgencc activity. In most instances they are crystalline and have good solubility in many organic solvents.

This differentiates them from the known bisalkylaminochloro triazines which are very difficulty soluble in most usual solvents. The novel compounds therefore are well adapted for spraying over fields from airplanes in the form of solutions in solvents.

The following, for instance, come into consideration as solvents for the compounds according to the invention: alcohols, ketones, hydrocarbons, halogenated hydrocarbons, for instance chloronaphthalene, mineral oils such as diesel oil, vegetable oils or mixtures thereof.

The novel triazine compounds can also be applied to solid carriers. As such, all known agricultural carriers come into consideration, for example: alumina, kaolin, kieselguhr, bentonite, talc, finely ground calcium carbonate, charcoal, wood four and the like. The active compounds can be admixed in dry form with the carriers. However, it is also possible to spray solutions or emulsions on or mix them with the carriers and drying the resulting mixtures. in order to obtain better adhesion of the active substances on the carriers, known adhesives, such as glue, casein, alginic acid salts and the like may be employed.

It is also possible, for example, to mix the triazine compounds, if it be desired, with carriers, with suspending agents and stabilizers to produce a paste or powder which then can be mixed with water to form a suspension.

Known anionic, cationic or nonionic substances can be emloyed as wetting agents, emulsifiers and stabilizers, such as, for instance, turkey red oil, fatty acid salts, alkyl aryl sulfonates, secondary alkyl sulfates, resin acid salts, polyoxyethylene ethers of fatty alcohols, fatty acids or fatty amines, quaternary ammonium compounds, lignin sulfonic acid, saponin, gelatine, casein, either alone or in admixture.

The following examples will illustrate representative preparations of compounds according to the invention, active compounds containing the same and their application.

EXAMPLE I 2-chloro-4-amino-6-( l-cyano-l-methyl-ethyl)-amino triazine.

l84.5 g. of cyanuric chloride was suspended in 750 ml. of acetone and the suspension cooled to C.; then 85.7 g. of alpha-amino isobutyronitrile (1.02 mol) were added gradually while maintaining a temperature not above C. Thereafter, a solution of 40 g. NaOH in 100 ml. of H,0 was added gradually, care being taken that the pH did not exceed 8. Then 200 g. of a 17 percent ammonia solution was added gradually without external cooling. The temperature gradually rose to 3035 C. The mixture was stirred until it reacted neutrally. The acetone was then drawn off under vacuum and water added to the residue. The resulting thick crystal paste was filtered off, washed with water, and dried under vacuum at 50C. Yield: 174.4 g. (82 percent oftheory) Thin layer chromatogram: 98 percent Analysis C H N Cl C,H,N,Cl calculated 1: 39.5 4.3 39.5 16.7 mo. wt. 2l2.5 found I: 39.7 4.4 39.5 l6.6

EXAMPLE 2 2-chloro-4-ethylamino6-( 1-cyano-l-methyl-propyl)-aminotriazine.

184.5 g. of cyanuric chloride was suspended in l liter of tctrahydrofuran and the suspension cooled to 0 C. While maintaining this temperature and stirring, l00 g. of alphaaminoisovaleronitrile were first added gradually and then 80 g. of 50 percent aqueous NaOH added gradually. The mixture quickly became neutral. The cooling was suspended and 90 g. of a 50 percent aqueous ethylamine solution was added, permitting the temperature to rise, and then again 80 g. of 50 percent aqueous NaOH gradually added thereto. The maximum temperature reached was 45 C. After processing analogously to example I, 240.5 g. of asnow-white product of amelting point of 139 to l4lC. was obtained.

Analysis:

C H N Cl C,,H,,N.Cl calculated 5 47.2 5.9 33 I19 mol. wt. 254 found 47.2 6 33.] NJ

2-ethylamino-4-( l-cyano-ethyl)-amino-6-chlorms-triazine of a melting point of l74 to 175 C. was produced analogously from cyanuric chloride, alpha-alaninenitrile and ethylamine.

EXAMPLE 3 2-methoxy-4-ethylamino-6-( l-cyanol 'methyl-ethyU-aminotriazine.

240.5 g. of 2-chloro-4-ethylamino-6-( l-cyanol methylethyl)-amino-triazine was added to 1 liter of methanol containing 54 g. of sodium methylate at 3035 C. The reac- -tion was weakly exothermic. The reaction mixture waskept at 30-35 C. for 4 hours and then at 60 C. for 1 hour. The solution then reacted neutral. The methanol was evaporated off under 'vacuum and the residue taken up in water and the crystals formed filtered'off, washed rwithwater andrdried. Yield:'227 g. Melting a point: l 38C.

Analysis:

C H N C JI NJ) calculated 11 50.8 6.8 35.6 mol. wt. 236 found Iv 50.7 6.9 35.7

2-ethylamino-4-(l-cyano)-ethyl-6-methoxy-s-triazine of a melting'point of 94-95 C. was prepared analogously from the corresponding -6-chloro compound.

EXAMPLE4 2-methylmercapto-4-fl-cyanoethylamino-6-( l -cyanol methyl-propyl )-amino-triazine.

, in-water. After filtering off, washing and drying, the resulting crystals, 284 g. of a white crystalline powder of a melting point of l l0l 12 C. was obtained.

Analysis:

6 H N (I C,,H,,N,s calculated a 49.5 51; 33.1 ".0 mol. wt. 29! found I: 49.7 5.8 33.6 [1.0

2-ethylamino-4-( l-cyano-ethyl)-6-methyl-mercapto-striazine of a melting point of 79-8l C. was prepared analogously-from the corresponding 6-chloro compound.

EXAMPLE 5 2-azido-4-methylamino-6( l-cyanol methyl-hexyl l-aminotriazine.

Analysis:

C H N C H,,N, calculated k 49.3 6.6 43.6 mol. wt. 289 found 5 49.7 6.8 43 3 2-ethylamino-4-( l-cyano-ethyl -amino-6-amino-triazine. of a melting point of 91-92 C. was prepared analogously from the corresponding 6-chloro compound.

EXAMPLE 6 2-isopropylamino-4-ethylamino-6-( l-cyano- 1 -methy1-ethyl anino-triazine.

An aqueous solution of 120 g. of isopropylamine in 600 ml. of ",0 was placed in a 2-liter autoclave and 240.5 g. of 2- chloro-4-ethylamino-6-( l-cyano- 1 -rnethyl-ethyl)-aminotriazine added thereto. After closing the autoclave it was heated to 100-l10 C. for 4 hours. After processing the reaetion mixture in a manner analogous to that of the preceding examples, 253 grams of a white crystalline product of a melting point of 9l92 C. were obtained:

2-propylmercapto-4-ethylamino-6-( l-cyano- 1 -methylpropyl)-amino-triazine.

224 g. of 2-propylmercapto-4,o-diehlorotriazane was dissolved in 500 ml. of acetone and 98 g. of a-aminoisovaleronitrile added slowly while cooling to 10 to C. and then a solution of 40 g. of NaOH in 100 ml. of 11,0. The pH of the solution was between 7 and 8. Then 90 g. of a 50 percent cthylamine solution and 100 g. of 40 percent NaOH in H,0 were added. The mixture was heated under a reflux condenser to 60 C. while stirring for 3 hours. The solvent was distilled off and the residue taken up in water. A thick crystal paste formed which was further washed and dried. Yield 282.5 g. corresponding to 96.3 percent of theory, melting point 7 l72 C.

Analysis: I mm 7 C H N S C,,H,,N.S calculated a 53.1 7.5 28.6 10.9 mol. wt. 294 found 52.8 7.2 28.8 l0.6

EXAMPLE 8 2-ethylmercapto-4-ethylamino-6-( 1 -cyano- 1 methl-ethyl)-amino-triazine.

21 g. of 2-ethylmercapto-4,6-dichlorotriazine was introduced into 100 ml. of acetone and 8.3 g. of a-amino-isobutyronitrile slowly added to such solution. Subsequently a solution of 4 g. of NaOH in 15 ml. of H 0 were added slowly. The temperature was C. Then 9.1 g. of a 50 percent solution of ethylamine were added at 40 C. and subsequently 4 g. of NaOH in ml. of H,0. The solution was then heated under reflux for 4 hours It reacted neutral at the end. The acetone was removed under vacuum and the residue taken up in water. Crystallization was completed in a short period of time. 24 g. of white crystals of a melting point of 126127 C. of a 91.2 percent yield was obtained.

EXAMPLE 9 2-chloro-4-methylamino-6-( l-cyano-cyclohexyl )-aminotriazine.

184.5 g. of cyanuric chloride were dissolved in 1 liter of tetrahydrofuran. The solution was cooled down to 0 C. and 124 g. of l-cyanocyclohexylamine dissolved in 250 ml. of tctrahydrofuran added slowly thereto. Thereafter, a solution of 40 g. of NaOH in 200 ml. of water was also slowly added. The mixture quickly became neutral. Then 180 g. of 50 percent cthylamine solution was added all at once. The temperature rose from 0 C. to 45 C. After 10 minutes the reaction of the solution was neutral. The tetrahydrofuran was then distilled off under vacuum and the residue was taken up in water. The crystals which formed were filtered off, washed and dried. The yield of white crystals was 247 g. of 92.7 percent of theory. Their melting point was l83-l 84 C.

.12. EXAMPLE 10 136.5 g. of acetone were placed in a 3-liter round flask and cooled to 5 C. Then 5 ml. of triethylamine was added and subsequently 650 g. of liquid hydrogen cyanide was gradually added from a cooled supply. The reaction was exothermic. After completion of the reaction the pH of the solution was adjusted to 2 with 50 percent phosphoric acid.

An autoclave was filled with 1,800 ml. of liquid ammonia and after closing the acetone cyanhydrin was pumped in. The temperature rose to 40 C. and the mixture was subsequently heated to 50 C. for 3 hours. After cooling down the contents of the autoclave were removed. The crude product was a lightyellow liquid. It was rendered water-free by treating it three times with solid KOH and then fractionally distilled under vacuum Ti T 36mins with a dephlegmator. At 48-50 C. under a pressure of 13 mm. Hg colorless alpha-aminoisobutyronitrile distilled over in a quantity of 1,756 g. (88.8 percent of theoretical yield).

The following alpha-aminonitriles were analogously prepared by this method:

EXAMPLE 1 1 64.2 g. (1.2 mol) of ammonium chloride was dissolved in 200 ml. of water and then 78 g. of potassium cyanide slowly was added thereto while being stirred and cooled. Thereafter, 86 g. of methyl isopropyl ketone (1 mol) was slowly added to the mixture at 15-20 C. and the mixture stirred for 2 hours at this temperature. Subsequently ammonia gas was passed through the mixture while stirring for 2 hours, the temperature being slowly raised to 50 C. After cooling down the mixture was placed in a separatory funnel and shaken out three times with ether. The ether extracts were united and dried with Na,SO and the solvent distilled off under vacuum. The residue was distilled over a small column under vacuum. The desired 1 -methyl- 1 -cyano-2-methyl-n-butylamine distilled over at 60-61 C. at a pressure of 12 mm. Hg as a water white liquiid. The yield was 86 g. or 76.7 percent of the theoretical yiel The remaining novel cyanoalkylamino triazines according to the invention shown in the table preceding the examples, as well as in the following examples, were prepared by methods analogous to those described in the above examples employing the appropriate amine, ammonia, azide,'alcoholate, alkyl mercaptide, cyanoalkylamine and halo-s-triazine as starting material. in the following parts" signify parts by weight.

EXAMPLE l2 10 parts of 2-methy1amino-4-(l-cyano-l-methyl-ethyl)- amino-t'a-chloro-triazine, 89 parts of bentonite. 1 part of finely divided pyrogenic silica, were together ground in a ball mill to a fine dust. The mixture could be applied as a dust.

EXAMPLE 13 A mixture of 10 parts of 2-ethylamino-4-( l-cyanol methyl-n-propyl)-amino-6-methoxy-triazine and 90 parts of kieselguhr were ground together to produce a dust of extreme fineness suitable for application as a dust.

EXAMPLE 14 A mixture of 20 parts of 2-isopropylamino-4-(l-cyano-lmethyl-ethyl)6-methylmercapto-triazine, 70 parts of chlorobenzene and 10 parts of an octylphenyl polyglycol ether produced from di-t-butyl phenol and about 10-12 mol of ethylene oxide (l-lostapal CV) was prepared. This mixture provided a stable dispersion upon admixture with water.

EXAMPLE 15 25 parts of 2-isopropylamino-4-( l-cyano-l-methylethyl)- amino-o-chlorotriazine was dissolved in 150 parts of cyclohexanone, 15 parts, of xylene andv 10 parts of a substituted naphthalene disulfonic acid such as Nekal BX. This mixture provided a stable emulsion upon admixture with water.

EXAMPLE 16 50 parts of 2-ethylamino-4-( l-cyano-l -methylethyl)-aminoo-azido-triazine were dissolved in 450 parts of kerosene. The solution can be used directly for spray applications.

EXAMPLE 17 10 parts of 2-methylamino-4-( l-cyano-ethy1)-amino-6- chloro-s-triazine, 89 parts of bentonitc and 1 part of finely divided silica were ground in a ball mill to a dust of extreme fineness. The mixture is suitable for application as a dust.

EXAMPLE 1s A mixture of 10 parts of 2-ethylamino.-4-( l-cyano-propyl)- amino--methoxy-s-triazine and 90 parts of kieselguhr was similarly ground in a ball mill to a dust of extreme fineness to provide a mixture suitable for application as a dust.

EXAMPLE 19 A mixture of 20 parts of 2-isopropyl-amino-4-(l-cyanoethyl)-amino-G-methyl-mercapto triazine, 70 parts of chlorobenzene and 10 parts of an octyl phenyl polyglycol ether (Hostapal CV, produced from di-t-butyl phenol and 10-12 mol of ethylene oxide). This preparation upon mixture with water gives a stable dispersion.

25 parts of 2-isopropyl-amino-4-( l-cyano-propyl)-amino-6- chloro-s-triazine were dissolved in 150 parts of cyclohexanone, 15 parts of chlorobenzene and 10 parts of a substituted naphthalene disulfonic acid, such as Nekal BX. The mixture upon admixture with water gives a stable emulsion.

EXAMPLE 21 50 parts of 2-ethylamino-4-(1-cyano-ethyl)-amino-6-azidos-triazine were dissolved in 450 parts of kerosene. The mixture can be sprayed directly.

EXAMPLE 22 The following tests were carried out to investigate the herbicidal activity of compounds according to the invention:

a. Preemergence soil treatment after seeding:

Various seeds were sown in soil in plastic dishes in a greenhouse maintained at 21 C. watered in the morning and in the afternoon, treated with a dispersion obtained by pouring a solution of the herbicide in equal quantities of water. Thereafter, the sprouting of the plants was observed with normal watering and after 2 weeks it was determined whether and herbicide to the soil was effected after sprouting. After 2 it was determined if and to what extent the plant growth had been reduced.

0. Leaf treatment: I p I The procedure as described under-(b') was followed except that the herbicidewas applied to the plant leaves rather than the soil.

The results of the tests are given in the following tables. The growth was evaluated according to a scale ranging from 0 to 9 in which 0 signifies normal growth and9 total destruction of the plant. I

The active substance concentration in the tests under (a) corresponded to kg./hectare and in tests under (b) and (c) to 10 kg./hectare and l kg./hectarc, using the following compounds:

1 2-amino-4-( l-methyl-1-cyano-ethyl)-amino-6-chlorotriazine 20 ll 2-methylamino-4-(1-methyl-1-cyano-ethyl-amino-6- chloro-triazine lll 2-ethylamino-4-( 1-methyl-l-cyano-ethyl)-amino-6- chloro-triazine lV 2-ethylamino-4-( 1-methyl-1-cyano-n-propyl)-amino-6- 25 chloro-triazine V 2-methylamino-4-( l-methyll -cyano-ethyl)-amino-6- azido-triazine V1 2-ethylamino-4-( l-methyll -cyano-ethyl)-amino-6- azido-triazine V11 2-ethylamino-4-(l methyl-l-cyano-ethy1)-amino-6- methylmercapto-triazine V111 2,4-bis-ethylamino-6-chloro-triazine 1X 2-ethylamino-4-isopropylamino-6-chloro-triazine Xg ethylamino 4 t-butylamino--methylinercapto-tgazine TABLE [Test 2.]

Rye Lin- Mus- Sugar Substance used Corn Oats grass Peas seed turd boots 4 9 8 6 J 0 U 0 s 8 s it u u 0 8 8 5 9 J at 0 8 8 5 1) it 5! 4 8 8 4' 9 1! u 4 7 7 4 U t) :1 6 J 9 7 9 n o 0 6 7 5 u n u 0 7 a s n n n 3 7 8 4 u u o TABLE [Test b] K Substance 115C 1 Rye Lin- Mus- Su used taro Corn Oats grass Peas seed turd best 10 4 9 8 7 9 1) {I I 1 0 g 4 u u u 8 10 0 8 5 3 .1 {I n H 1 0 8 4 2 a) u u 10 1 n u 5 o u o In 1 0 g 7 5 9 1| n 10 0 s s 5 u u 0 IV r .v l 1 1 1 0 7 s 3 t .1 1 10 2 8 8 4 I J u l 1 0 7 4 0 I w 1.: 1 2 s s a 1 n "i (1) 1 8 7 1; *g 3; 1 1 i i VII I) u 21 Comparison; 5 10 3 r 4 5 n u 1.

VIII

1 0 2. 2 g s 3 J I IX 2 5 8 1| u 10 3 S 1) 6 1| 2| I X i. 7 g rq TABLE [Test c] Substance hec- Rye Lm- Mussugar used tare Corn Oats grass Peas seed tard beet l0 2 8 J 1 .1 u u I 1 0 s 4 0 ti u s 10 0 ii 8 3 t) .1 n H 1 i 5 4 n 7 l. 7

Oats, mustard and linseed were sown in seed pans filled with earth. After the plants had reached a height of 8 cm. they were treated with an 0.5 percent emulsion of 2-ethylamino-4-( lcyanol -methyl-ethyl)-amino-6-methoxy-triazine. After l8 days all plants were destroyed.

EXAMPLE 24 The following further tests were carried out to investigate the herbicidal efficiencies of the compounds according to the invention:

a. Preemergence soil treatment after seeding:

Seeds of test plants were sown in narrow strips in plastic I flats (38xl3X6 cm.) filled with John lnnes potting compost.

10 7 S 1 8 J 9 1 0 3 3 (l 8 U 8 10 4 7 .I 3 .I J U l 0 1 1 1 B J l 10 4 7 9 .2 8 9 ti 1 0 4 4 0 7 ti 3 1t) 6 8 J 3 .l .l U 1 l 4 2 0 7 7 ll Comparison:

t 0 4 ti 1 ti 8 7 "1 1 o 2 4 n 4 (a 7 I l 10 1 5 7 3 s u 7 "I 1 u 3 5 2 5 a ii I t 10 3 7 8 3 J l I 1 0 4 4 0 u 9 s10 EXAMPLE 23 stance and the PD" determined therefrom, that is. the active substance concentration providing a percent reduction of the plant growth.

b. Post-emergence treatment:

The seeds were sown in plastic plates 9 cm. in diameter. After sprouting the plants were sprayed with the herbicidal agent at various concentrations. After l0 days the phytotoxicity and PD were determined as under (a).

When agropyron repens was used as the test plant, the sprouts were cut off at the surface of the soil and the further growth after 3 further weeks determined The PD values for the various plant vertices tested are given in the following tables I (according to a) and ll (according to b).

The compounds according to the invention tested were of the formula wherein R, R, R and X have the significance indicated in the tables for the compounds tested.

In comparative tests 7a, 12 and 18, the group indicated under R and R replaces the group in the compounds according to the invention.

TABLE 1 [Test :1]

Finger Fox R R R Com Wheat Barley Rice grass tail CzHs CH3- CHa- 5 0. 21 0. 16 0.1 0. 1 0. 1 @2115 CHr- C2H5 5 '2. 6 3. 6 2. 2 l. 6 1. 2 C2Hs CI-Ir- CH: 1. 2 0.21 0. 22 0. 1 0. 1 2H5 011 CH;- 0. 26 0. 1 0. 1 0. 1 0. 1 H CH CHa- 5 0. 84 0. 23 0. 1 0. 1

r, 01 CH3- 7 Cl (CII7)3OCHJ Cllrour 5 0. 2!) 0. 2H 0. 2.) 0. 1 7n. CI 02115 (NIICa'lh-i' 5 0. 8'3 1. 1 0. G

Barn- Chennyard Sugar Knot odium Test No grass 3 Cotton beet (lubluigu Plantain Chicory grass Muyweed Clover album 1 0. 42 0.1 0.1 0. 1 0.1 0.1 0.1 2. ))5 1. 0 0.50 0. 80 0. J5 0. 1 0. 3.) 0. 1 3. 0. 1 5 0. 1 0.1 0.16 0. 1 0. 1 0. 1 0. 1 4. 0.1 1. 3 0. 1 0. 1 0. 1 0. 1 0.1 0.! 0.] 5. 0. 19 0. 79 0. 1 0.5 0.1 0. 1 0. 1 0. 1 0. 1 6- 1. 6 5 0.5 0. 42 0.21 0. 22 0. 0. 18 7, 0. 22 4. 7 0. 23 0. 1 O. 16 0. 18 0. 1 0. 1 0. 12 7a 0. 56 5 0. 35 0. 2 0. 2 0. 2

1 Not tested. 2 Comparison. 3 ECILi'IIOChlOlZ cruagulli.

TABLE II [Test 1)] Finger R R- R Corn Wheat. Barley Rico grass Foxtail CzIIa- CIIs- Clla 0. 76 0. 18 0. 1 (l. 22 0.68 0. 1 CzH5- C1I C2IIr- 1. 8 0. 62 0. 52 0. 65 0. B0 0. 37 C2H5 CII CH 0. 0. 20 0. 1 0, 25 O 15 0.] 02115 C11 C[I 0. 7 0. 1 0. 1 0.16 0. 1 02115 (0II2)'7CN2 5 2. 7 1. 1 3. ti 5 1.7 II CII CH 5 (1.48 0. 27 0. 58 0 DU 0. 34 11 0113" CII 0.11) 0.11 0.1

---(C1l9)a00llu CH5 CH3 5 0. 34 0.13 (I. 58 U. 27 (l.1 -(C112)3OC1[3 C115 C11; 0.17 0.07 0.2; C211 NlICfln-i 5 0.1 0, 3 0. 45 n Cai n CH: CH: 7. 1 2.3 H CH; CzHs 7.4 5. CH CH CzHs 7.9 3.9 C: s CH1 01H; 8. 2 5.4 Call-r1 CH: Calls 7. 7 3. 9 C711; CH: CgHrn 7.6 3. 1 CH1 CH3 CsH1-l 7.4 3.4 C2115 CH: CgHrl 7.6 3. 0 (,gllrl C11: CaH1-l 7. 4 2. 3 C11; C2115 C H; 7.4 4.6 C2115 C7116 CgHs 7.4 4.9 (1 111-1 C71 1: C1115 7.7 2. 1 CH; CgIIn-Xt 6. 9 0. 9 (3 11 CH3 CH1 7. 4 4. 3 ill: CH: 0511114 7. 0 l. 3 C1115 C113 CsHn-l 5.7 1.3 (,lhCll=Cll CH; CH; 7.4 4. 6 (CllihSClls CH: CH; 6.0 1. 1 (0111070011: CH: CH; 7.4 4. 0 CIIqClIzOll CH; CH; 7. 0 0 ()Czlls CH: CH: 7. 1 3. 4

NII (in. 7. 0 1. 9

NH can 7.4 2. 4

NII (3111 4 o. 7 1. 3

UsIh-l H CH: 7. 7 5. 1

'R=C21l5.

TABLE 4 lX=SCzHt; R==H] Pro-emer- Leat genes soil R 1?. R treatment treatment C7115 CH3 CH3 7. 7 4. 1 Calls CH; 02115 7. 4 2. 6

TABLE 5n [X=OCH7; R =H] Leaf Pro-emertreatgence soil 1t R R ment treatment 11 CH: CH: 7. 4 6. 0 (Ill: C11: C11: 7. 6 0. 6 Calls C11: C11: 7. 8 (l. 8 (331114 (111: C11: 8.0 6. 7 II (311: Call; 7. 7 5. 1 (1115 C111 C211; 7. 7 6. 4 (Ill: C11: (3 111-1 7.4 4. J (7 11:, C11: Csllrl 8.0 4. G (Igllrl U11: Cally-l 7. 6 3. (1 (ill: C211 C1115 7.3 4.3 alli (1711 C9115 7. 3 4.4 (1"; C": C llu-ll 11.11 2. 6 mil. on. (31h 7.4 4.3 ((lllflsUV-ll: (11; U11] 11.11 4.11 llrhMzlls 11: ll; 7.!) 3.1 (h ll I1 (711: 7.4 (L0 (UlltllUUll; 11 C11: 11.0 4.3

TAU LE 51) [X=OCall R 11] Leaf Pro-emertreatgence soil it" R R ment treatment C211 C11: C11: 7. 7 6. 7 C2115 CH: 0111; 7. U 4. 3 21 5 C113 C211; 6. 4 l. 3

'X=N1IC211 TABLE 6.-KNOWN COMPOUNDS Substltuent in position Leaf Pre-emertreatgenes soil 2 4 G ment treatment Cl -N11C2l1; Nll(CIImCN 2. 4 2.0 Cl ---Nl1(Jall -l -Nl[(C1lz)zCN 4.1 1.0 N] -SU1I: NII(CH);CN .2. J l. 0 Cl --Nl[Cz1l NC112115 5.6 3.3 C1 "-N1[C7114 NClls1l1-i 5.!) 4.1 Cl -Nl1Czl1 NlICll CN 1. 6 1. 6 Cl -NllCa1l7-l "NIH/MAIN 0.6 0.3 CI -N1l'.' NllCllzCN 1.1 0 U1 NllUlln "NllCllzCN 2.1 0.4 NllCzll -NllU((llh)- (T()()ll (l 0' l NlHHll -Nll(.(()ll:i)-;(-()Nll- 0 0 NllUull -NllUtUllahVUUCllu 0-1 -2 20 EXAMPLE 26 The following procedure-was used to determine the ability of the compounds according to the invention to decompose in soil:

Air dried loam was brought to a moisture content of 20 percent. The active substances tested were introduced into 2 kg.

portions of such soil as a solution in 5 ml. of acetone to provide a concentration of active substance corresponding to 0.3 kgJhectare. The treated soil was stored in covered plastic containers for varying lengths of time at a constant temperature of 2 I C.

After various periods of storage, samples were removed and placed in pots in which sugar beet seedlings were transplanted. The pots were watered from below and held at 21 C. in a greenhouse. The phytotoxiciq was determined 1 week after the transplanting. The following table gives the percentage of the plants destroyed.

(comparison) EXAMPLE 27 The herbicidal activity of the following compounds was tested:

l 2-ethylamino-4-( l-cyanoethyl)-amino-6-chloro-striazine ll 2-isopropylamino-4-(l-cyanoethyl)-amino-6-chloro-striazine 2-ethylamino-4-cyanomethylamino-o-chloro-triazine (prior art) lV 2-ethylamino-4-(2-cyanoethyl)-amino-6-chloro-striazine (prior art) V 2,4-bis-ethylamino-6-chloro-s-triazine (prior art) The tests were as follows:

a. Post-emergence soil treatment:

Various seeds were raked into soil in a greenhouse maintained at 21 C. After sprouting, a dispersion obtained by pouring a solution of the herbicide in equal quantities of water was applied to the soil. After 2 weeks it was determined if and to what extent the plant growth had been reduced.

b. Leaf treatment:

The procedure described under (a) was followed except that the herbicide was applied to the plant leaves rather than to the soil.

The results of the tests are given in the following tables. The growth was evaluated according to a scale ranging from 0 to 9 in which 0 signifies normal growth and 9 total destruction of the plant.

The active substance concentration in each instance was i kgJhectare.

Ill

TABLE Substance Rye- Lln- Mus- Sugar tested Corn Oats grass Peas seed turd beet (a) Post-emergence soil treatment 1 7 7 (i U .l J 1 7 6 5 i) J J 0 0 0 1 4 5 l 0 (l 1) 3 ii 7 l 3 .2 4 It 7 ti (h) Leaf treatment 0 7 7 0 0 o .l 0 ti 2 o a T .l 0 o it n o r. 1. o 2 o o 4 2 n 0 .1 4 ll 4 li T EXAMPLE 28 A young mixedflora of lolium perenne, digitaria san-' guinalis, alopecurus'pratensis, agr'opyren repens and planta'go The table indicates that, for-instance, compounds V4 and VShave considerably stronger selectivity in cereals such as wheat and-barleythan the comparison substance VI. It can furthermore be 'noted that compounds V2 and V3 in comlanceolata was's ra ed once'with a :5 ercent emulsion oi the following subgmgcey p panson w1thVl have a stronger actlon agamst crab grass and i. 2'ethylamino 4 y y y barnyard grass while maintaining their selectivity incorn. tnazine i EXAMPLE 30 2. 2-ethylam|no-4-( l-cyanoethyl)-am1no6-methyl-mercapm 2-ethylam1no-4-(,l.-cyanoethyl)-amino-6-chloro-s-triazine 2 methy|amim 4 (1.cyanopmpyi) amino-6-azido-swas tested as to its ability to decompose in soil using the "iazine method'disclosedin example 26 but using a concentration of Afterq g-d ll l t were 'totally destroyed. active substance corresponding to. 0.0l kg.-/hectare. The half y y value time forsuch a compound was 215 weeks. in com- EXAMPLE 29 I 5 parison, the half value time of 2-ethyl-amino-4- A mixed flora of corn, wheat, barley, cotton,.di'gitaria san- 3223;222:22 g fi when aged ""4"" guinalis (crab grass), plantago lanceolata (pla'ntain), cichori- 1 l I was wee um endivia (chick'ory), chinochloa crus-galli (barnyard -T f l ff grass), amaranthusretroflexus (.pigweed'),'cabbage and sugarer i a composmfm comPnsmg an e acme beets was treated prior to emergence with vafious ,mazines amount of a cyanoalkyl-amlno subst1tuted tnazme of the forand compared with-a known commercial product. 'lneach'in mula stance the quantity of herbicide (-kg.'/hectare) which was' required for destruction of i0, 50-and'90 'percent of the plants. N}

Substance (VI), 2*ethylamino-4 isopropylamino-6-chlorotriazine was selected as the comparison substance. C

All compounds corresponded to the-formula II R1 \N-(!1 CNi[-U-CN L a v b H N ll N N 5 LL whereinX'is selected from the group consisting of halogen,-

lower alkoxy, lower alkyl mercapto, 1v Ee'irlghydrogen lower alkyl. lower alkenyl, substituted lower 35. alkyl or subs'titutedloweralltenyl in which latter two'jgrou'ps the substituents-are '-Ol-l, -OR, -SR-or -C-N,- R being lower al- Substunco No. R -1R R kyl,'and wherein one of R and R is alkyl or alk'enyl having v1 Cl NHCH NHCSHH from one to eight carbon atoms and the other is-hydrogen. V2 C1 NIICflh NII-Cfl-CN alkyl or alk enyl having from one to eightcarbon atoms. and CH where|n "R" and R together'with the ad oining carbon atom 3 may form a Sato 7 member cycloalkyl ring; and (b') an agriculva Cl NHC2HB NIIC1ICN turallyacceptablecarrier forsaid triazine'compound.

gm 2. The composition of claim I, which is in the'to'rm of a W C! no H NH CH CN sprayablesolution," the carrier being an organic solvent for N 2 i said triazine compound.

, 5111-11 3/Th'e composition of claim I, whereinrthe carrier is in solid \'5 01 1111011, NHCII-CN H i 4. The herbicidal composltlon of cla1m3. wherein the solid 3 {carrier is selected from the .group consisting of alumina, V0 C1 NIIClHi NII'C II'' N 5O l kaolin, kieselguhL'bentonite; talc, finely' ground calcium car- SHH bonate, charcoal and wood flour. p 5. The composition of claim I, which is in the form of a v 0 NHCzH NH CH CN suspensiomthe carrier beinga su'spensionm'edium.

I H: 6; The composition of claim 5, which includes atleast one Th0 msultq of the tests are given in the following 55 of the following: stabilizers, wetting agents,iemulsifiers and adtablc: besives' TA-BL'E Dig. Ilunt Sugur Nu. llurlcy Cotton sung. lune Clch Echln. Allllll. (,ublmgv lm-l.

' 0.211 3.4 0.215 02 02 0. 23 0.. 0. 2 0.2 1.. 1.1 5- 0.0 02 02 0. 0.: 0.: 0. 35 5 2. 7 0. 2s 0, 48 4.'2 0. 2 0. 211 0. 0 0.05 0.04 0. 03 0. 03' 0.03 0. 03 00: 00: \"2 0. ()8 0. 04 0.07 0. 04 0. 04 0.12 01): 0. 02 l. 0 0. 06 0. 46 0. 12 0.13 (1.45 0. 03 0. 0G 0. 14 0. 04 0. 1 0. 05 0. 05 0. '00 0. 08 0. 05 0. 05 #2 s 3% 3% 335 3%? 3% 8'5? 3"? L l 0.411 1.7 0.11 0.1 0. 11 0.15 0.00 0. 11 0.11 -1 i 2 0 g. 52 81}: 0 2g 0 00 11 0. 11 0.11 1.5 0.2 0.2 0: 11 0. '14 03? 0: i11 \5. 4 0 3a Z0 8. 10 0.11 0.111 0. 1

. .7 1 .02 0.211 0.25 0.1 I 0. 21 0.35 00.) 0.1 0. 11 0. 11 0.00 0.-1| 0. 11 \1. -0.7 1.115 0. 43 0.10 0. 11 0.11 0.011 0.11 '0. 11 2. 4 -1 2. 2 0. 2-1 0.15 -1. 2 0. 15 0. :5 0. 11; 0. 1 0. 7 0. 05 0. 05 0. 05 0, 05 w \o n 05 (0 1m (0, 0'1 00! 7. The composition of claim l wherein the compound both R and R are ulltyl or alkenyl having from one to eight carbon atoms and wherein R and R together with the adjoining carbon utom may form a live to seven member cycloalkyl ring.

it. The composition of claim I, wherein in the triazine compound one of R and R is hydrogen and the other is lower alkyl. lower alkenyl, substituted lower alkyl or substituted lower alkenyl, the substituents in the latter two groups being as defined in claim I. I

9. The composition of claim I, wherein in the triazine compound X is halogen.

10. The composition of claim I, wherein in the triazine compound X is chlorine.

ll. The composition of claim I, wherein in the triazine compound X is chlorine, and in which one of R and R is hydrogen and the other is lower alkyl, lower alkenyl, substituted lower alkyl or substituted lower alkenyl, the substitutions in the latter two groups being as defined in claim I, and in which both R and R are alkyl or alkenyl having form one to eight carbon atoms and wherein R and Rftogether with the adjoining carbon atom may form a live to seven member cycloalkyl ring.

12. The composition of claim 1, wherein the tria'zine compound is 2-chloro-4-ethylamino-6-( l-cyanol -methyl-ethyl amino triazine.

13. The composition of claim I, wherein the triazine compound is 2-chloro-4-ethylamino-6-( l -cyanol -methylpropyl)-amino-triazine.

14. The composition of claim I, wherein the triazinc compound is 2-chloro-4-methylamino-6-( l-cyanol -mcthylethyl)-am ino-triazine.

15. The composition of claim I, wherein the triazine compound is 2-methoxy-4-ethylamino-6-( l-cyano-l-methylethyl)-amino-triazine 16. The composition of claim 1, wherein the triazine compound is 2-methyl-mercapto-Lethyl-amino-6-( l-cyanol methyl-ethyl)-amino-triazine.

17. The method of controlling the growth of plants comprising applying a composition as defined in claim I to the plants or to the soil prior to or after emergence of said plants.

i t b 

3. The composition of claim 1, wherein the carrier is in solid form.
 4. The herbicidal composition of claim 3, wherein the solid carrier is selected from the group consisting of alumina, kaolin, kieselguhr, bentonite, talc, finely ground calcium carbonate, charcoal and wood flour.
 5. The composition of claim 1, which is in the form of a suspension, the carrier being a suspension medium.
 6. The composition of claim 5, which includes at least one of the following: stabilizers, wetting agents, emulsifiers and adhesives.
 7. The composition of claim 1, wherein the compound both R3 and R4 are alkyl or alkenyl having from one to eight carbon atoms and wherein R3 and R4 together with the adjoining carbon atom may form a five to seven member cycloalkyl ring.
 8. The composition of claim 1, wherein in the triazine compound one of R1 and R2 is hydrogen and the other is lower alkyl, lower alkenyl, substituted lower alkyl or substituted lower alkenyl, the substituents in the latter two groups being as defined in claim
 1. 9. The composition of claim 1, wherein in the triazine compound X is halogen.
 10. The composition of claim 1, wherein in the triazine compound X is chlorine.
 11. The composition of claim 1, wherein in the triazine compound X is chlorine, and in which one of R1 and R2 is hydrogen and the other is lower alkyl, lower alkenyl, substituted lower alkyl or substituted lower alkenyl, the substitutions in the latter two groups being as defined in claim 1, and in which both R3 and R4 are alkyl or alkenyl having from one to eight carbon atoms and wherein R3 and R4 together with the adjoining carbon atom may form a five to seven member cycloalkyl ring.
 12. The composition of claim 1, wherein the triazine compound is 2-chloro-4-ethylamino-6-(1-cyano-1-methyl-ethyl)-amino triazine.
 13. The composition of claim 1, wherein the triazine compound is 2-chloro-4-ethylamino-6-(1-cyano-1-methyl-propyl)-amino-triazine.
 14. The composition of claim 1, wherein the triazine compound is 2-chloro-4-methylamino-6-(1-cyano-1-methyl-ethyl)-amino-triazine.
 15. The composition of claim 1, wherein the triazine compound is 2-methoxy-4-ethylamino-6-(1-cyano-1-methyl-ethyl)-amino-triazine
 16. The composition of claim 1, wherein the triazine compound is 2-methyl-mercapto-4-ethyl-amino-6-(1-cyano-1-methyl-ethyl)-amino-triazine.
 17. The method of controlling the growth of plants comprising applying a composition as defined in claim 1 to the plants or to the soil prior to or after emergence of said plants. 